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Transcript
Organometallic Compounds: Alkyllithium Reagent Compounds that contain carbon-metal bonds are called organometallic compounds. . . Organometallic Compounds: Grignard Reagent . . Victor Grignard Nobel Prize (1912) . . . . RLi and RMgX as Strong Bases/Nucleophiles . . . . Reactions of RMgX with Epoxides . . Reactions of RMgX with Carbonyl Groups . . Alcohols from Carbonyls and Grignard Reagents Grignard reagents react with formaldehyde to give a primary alcohol . . Grignard reagents react with all other aldehydes to give secondary alcohols . . Grignard reagents react with ketones to give tertiary alcohols . . Alcohols from Carbonyls and Grignard Reagents Esters react with two molecules of Grignard reagents to form tert-alcohols . . 2 Restrictions on the Use of Grignard Reagents . . The Grignard reagent is a very powerful base/nucleophile. Thus, it is not possible to prepare a Grignard reagent from an organic group that contains an acidic hydrogen (any hydrogen more acidic than the hydrogen atoms of an alkane or alkene). . . Restrictions on the Use of Grignard Reagents . . . . Synthetic Plans Based on Grignard Reaction . . Retrosynthetic Analysis Synthesis Synthetic Plans Based on Grignard Reaction . . Retrosynthetic Analysis Synthesis Synthetic Plans Based on Grignard Reaction . . Retrosynthetic Analysis Synthesis
